Chiral salen-metal complexes are among the most versatile asymmetric catalysts and have found utility in fields ranging from materials chemistry to organic synthesis. These complexes are capable of inducing chirality in products formed from a wide variety of chemical processes, often with close to perfect stereoinduction. Salen ligands are tunable for steric as well as electronic properties, and their ability to coordinate a large number of metals gives the derived chiral salen-metal complex very broad utility in asymmetric catalysis. This review primarily summarizes developments in chiral salen-metal catalysis over the last two decades with particular emphasis on those applications of importance in asymmetric synthesis.